Can not fully sync my iPhone on my MBP, please help...

[iMerlin]

Hey all, I just recently ran into this issue. I have 2 iPhone I sync with my MBP. One 3g and one 2g. They are both running the latest 2.2 fw. Also I am up-to-date on iTunes.

This issue has been happening on my 3g iPhone since before the iTunes and iPhone updates last week. I figured the updates might help but they didnt.
So I plug my phone in to sync and iTunes sees my phone and I start to sync. It gets through my music, then my videos (sometimes) then it gets to the screen that says Syncing Merlin's iPhone... and it just sits there. I can let this run for hours and it still says the same thing.

I have no idea what to do here. So I tried a restore and now it wont put my pictures back on. It just sits at the Syncing screen. It loads up all my music, movies and apps, then goes to the Syncing screen and never makes it to my pictures.
I also noticed that some of the pictures I saved from emails into my camera roll are now blurry when before they were perfect.
Also, my iTunes library is stored on my Drobo which I connect to over my Airport. Ive never had an issue with this before so I dont think that is the problem. But I did notice that iTunes wasnt displaying the number of pictures in the folders. Which it used to.

So I remapped the picture folders and the amount appeared. I tried to sync again and still...

So I did some searching on the net and on this forum and didnt find much. I found one post which talked about doing something in iSync so I tried that and still nothing. That post was about iTunes getting stuck on the contacts sync, mine doesnt get stuck there.

So anyway, I thought this all pointed to my iPhone. So my mom came over this weekend, she has the 2G iPhone. I tried putting some new pictures on her iPhone and the same thing happened. It just sits at the syncing screen. So this leads me to think it is either a problem with iTunes or my MBP.

If anyone has any ideas I would really appreciate it. Im reluctant to delete iTunes and reinstall that since it would take me forever to get my library back the way it is now. Unless Im wrong about that. If I reinstall iTunes will it remember all of my album art and stuff like that? Is that all saved in the library database file? I would hate to have to reload all my TV Show art and movies, that wasnt fun... Oh and, I cant take it to a genius since my entire library is on my Drobo.

Thanks in advance for any help.

 

[iMerlin]

So Im starting to think this might be a problem with MobileMe. I signed up for the free trial a couple of weeks ago, now Im having this issue. So I closed my new Mobile me account and deleting the account from my iPhone. I then signed out of the account on my MBP and cleared the sync history from iSync. And Im still having an issue. Ive been working on this problem for 2 fricken days. I have no idea what to try next other than a fresh install of iTunes.
So does anyone know if I will lose all my lovely artwork if I do delete and reinstall iTunes??

EDIT: So it looks like its a picture problem. I just told iTunes not to sync pics and it completed the sync. I then imported a month of pictures into iPhoto and resyncd and this time it worked. So anyone know a reason why it wouldnt let me sync pics stored on my Drobo? All of my music and videos are on that same Drobo and that works just fine. Im confused.